tert-butyl (4R,5S,9S)-5-hydroxy-9-(methoxymethoxy)-4-methyl-3-oxoundecanoate | 1187934-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (4R,5S,9S)-5-hydroxy-9-(methoxymethoxy)-4-methyl-3-oxoundecanoate
• CAS: 1187934-85-5
• 化学式: C₁₈H₃₄O₆
• 分子量: 346.464
• InChiKey: HDTFZRGZCFHQSV-ILXRZTDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R,5S,9S)-5-hydroxy-9-(methoxymethoxy)-4-methyl-3-oxoundecanoate 在 二乙基甲氧基硼烷 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 8.0h， 以78%的产率得到tert-butyl (3R,4R,5S,9S)-3,5-dihydroxy-9-(methoxymethoxy)-4-methylundecanoate
  参考文献：
  名称：

  Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone

  摘要：

  The total synthesis of lactone I has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.06.008
• 作为产物：
  描述：

  醋酸叔丁酯 、 methyl (2R,3S,7S)-3-hydroxy-7-(methoxymethoxy)-2-methylnonanoate 在 lithium diisopropyl amide 、 水 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到tert-butyl (4R,5S,9S)-5-hydroxy-9-(methoxymethoxy)-4-methyl-3-oxoundecanoate
  参考文献：
  名称：

  Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone

  摘要：

  The total synthesis of lactone I has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.06.008

文献信息

• Stereoselective total synthesis of polyketide lactone, (3R,4S,5S,9S)-3,5,9-trihydroxy-4-methylundecanoic acid δ-lactone
  作者：Gowravaram Sabitha、Peddabuddi Gopal、Jhillu S. Yadav

  DOI：10.1016/j.tetasy.2009.06.008

  日期：2009.7

  The total synthesis of lactone I has been described. The convergent asymmetric synthesis relies on the use of an Evans' syn-aldol, chain extension with lithio tert-butyl acetate, and the stereoselective reduction of a ketone as the key reactions. (C) 2009 Published by Elsevier Ltd.